4′-Bromo­methyl­bi­phenyl-2-carbo­nitrile

Song, Q.-B.; Li, Y.-Z.; Qi, C.-Z.; Shen, T.-H.; Wang, H.-B.

doi:10.1107/S1600536803025571

4′-Bromomethylbiphenyl-2-carbonitrile

Q.-B. Song, Y.-Z. Li, C.-Z. Qi, T.-H. Shen and H.-B. Wang

In the title compound, C₁₄H₁₀BrN, the dihedral angle between the two aromatic rings is 48.34 (14)°. Weak C—H

Br and C—H

N interactions are the principal intermolecular forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025571/ob6317sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025571/ob6317Isup2.hkl Contains datablock I

CCDC reference: 227889

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.045
wR factor = 0.088
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2284
           Count of symmetry unique reflns         1319
           Completeness (_total/calc)            173.16%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       965
           Fraction of Friedel pairs measured     0.732
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4'-Bromomethylbiphenyl-2-carbonitrile top

Crystal data top

C₁₄H₁₀BrN	F(000) = 2176
M_r = 272.14	D_x = 1.538 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1496 reflections
a = 47.219 (12) Å	θ = 2.4–20.6°
b = 24.229 (6) Å	µ = 3.47 mm⁻¹
c = 4.1085 (10) Å	T = 293 K
V = 4700 (2) Å³	Prism, colourless
Z = 16	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2284 independent reflections
Radiation source: fine-focus sealed tube	1610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −58→52
T_min = 0.43, T_max = 0.50	k = −29→24
6379 measured reflections	l = −5→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2284 reflections	Δρ_max = 0.44 e Å⁻³
145 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 965 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (15)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

21.9209 (0.0998) x - 0.1847 (0.0528) y - 3.6388 (0.0046) z = 5.4707 (0.0434)

* 0.0016 (0.0037) C2 * -0.0013 (0.0040) C3 * 0.0003 (0.0040) C4 * 0.0003 (0.0036) C5 * -0.0001 (0.0040) C6 * -0.0009 (0.0040) C7

Rms deviation of fitted atoms = 0.0009

16.4269 (0.1123) x + 2.4815 (0.0646) y + 3.8288 (0.0040) z = 7.6557 (0.0414)

Angle to previous plane (with approximate e.s.d.) = 48.34 (0.14)

* 0.0051 (0.0039) C8 * 0.0028 (0.0049) C9 * -0.0088 (0.0057) C10 * 0.0066 (0.0054) C11 * 0.0015 (0.0046) C12 * -0.0072 (0.0040) C13

Rms deviation of fitted atoms = 0.0059

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br	0.272011 (12)	0.65748 (2)	0.49307 (17)	0.0614 (2)
C1	0.30571 (10)	0.62629 (18)	0.2846 (16)	0.0509 (14)
H1A	0.3236	0.6460	0.3975	0.061*
H1B	0.3025	0.6377	0.0715	0.061*
C2	0.30797 (10)	0.56493 (19)	0.3227 (12)	0.0406 (13)
C3	0.28709 (10)	0.53046 (19)	0.1995 (15)	0.0462 (13)
H3	0.2705	0.5489	0.1014	0.055*
C4	0.29008 (10)	0.47354 (18)	0.2199 (15)	0.0445 (12)
H4	0.2747	0.4522	0.1438	0.053*
C5	0.31403 (10)	0.45058 (19)	0.3654 (11)	0.0382 (13)
C6	0.33463 (9)	0.48542 (18)	0.4878 (16)	0.0431 (12)
H5	0.3529	0.4723	0.5831	0.052*
C7	0.33114 (10)	0.54225 (18)	0.4641 (15)	0.0419 (12)
H6	0.3468	0.5646	0.5513	0.050*
C8	0.31705 (10)	0.38964 (19)	0.3880 (12)	0.0396 (13)
C9	0.29460 (11)	0.35779 (18)	0.5044 (18)	0.0547 (14)
H9	0.2760	0.3730	0.5305	0.066*
C10	0.29691 (13)	0.3008 (2)	0.5284 (19)	0.0725 (19)
H10	0.2810	0.2816	0.6064	0.087*
C11	0.32143 (12)	0.2747 (2)	0.4442 (19)	0.0704 (18)
H11	0.3222	0.2371	0.4892	0.084*
C12	0.34392 (12)	0.3043 (2)	0.3272 (14)	0.0566 (17)
H12	0.3607	0.2881	0.2890	0.068*
C13	0.34199 (10)	0.36196 (19)	0.2958 (14)	0.0437 (14)
C14	0.36506 (12)	0.3904 (2)	0.1625 (13)	0.0463 (15)
N1	0.38449 (10)	0.41217 (16)	0.0496 (14)	0.0642 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0633 (4)	0.0500 (3)	0.0709 (4)	0.0116 (3)	−0.0080 (4)	−0.0071 (4)
C1	0.056 (3)	0.042 (3)	0.055 (4)	0.001 (2)	−0.007 (3)	0.005 (3)
C2	0.040 (3)	0.040 (3)	0.042 (3)	−0.005 (2)	0.005 (3)	0.003 (2)
C3	0.037 (3)	0.049 (3)	0.052 (4)	0.006 (2)	−0.006 (3)	0.004 (3)
C4	0.039 (3)	0.045 (3)	0.049 (3)	−0.004 (2)	−0.006 (3)	−0.009 (3)
C5	0.035 (3)	0.041 (3)	0.039 (3)	0.002 (2)	0.008 (2)	0.000 (2)
C6	0.039 (3)	0.044 (3)	0.046 (3)	0.001 (2)	−0.005 (3)	−0.003 (3)
C7	0.038 (3)	0.043 (3)	0.044 (3)	−0.003 (2)	−0.006 (3)	−0.001 (3)
C8	0.035 (3)	0.039 (3)	0.045 (3)	−0.004 (2)	−0.001 (2)	−0.001 (2)
C9	0.047 (3)	0.046 (3)	0.071 (4)	0.002 (2)	0.008 (4)	0.002 (4)
C10	0.076 (4)	0.048 (3)	0.094 (5)	−0.016 (3)	0.021 (5)	0.010 (4)
C11	0.071 (4)	0.037 (3)	0.103 (5)	0.000 (3)	0.010 (5)	0.004 (4)
C12	0.064 (4)	0.036 (3)	0.070 (5)	0.009 (3)	0.000 (3)	0.000 (3)
C13	0.044 (3)	0.037 (3)	0.051 (4)	−0.003 (2)	−0.004 (3)	0.001 (3)
C14	0.042 (3)	0.042 (3)	0.055 (4)	0.005 (2)	0.007 (3)	−0.002 (3)
N1	0.052 (3)	0.054 (3)	0.086 (4)	0.001 (2)	0.009 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Br—C1	1.959 (5)	C7—H6	0.9830
C1—C2	1.499 (6)	C8—C9	1.396 (6)
C1—H1A	1.0754	C8—C13	1.407 (6)
C1—H1B	0.9305	C9—C10	1.389 (7)
C2—C7	1.355 (6)	C9—H9	0.9577
C2—C3	1.388 (6)	C10—C11	1.364 (7)
C3—C4	1.389 (6)	C10—H10	0.9396
C3—H3	0.9877	C11—C12	1.369 (7)
C4—C5	1.395 (6)	C11—H11	0.9303
C4—H4	0.9453	C12—C13	1.407 (6)
C5—C6	1.383 (6)	C12—H12	0.8997
C5—C8	1.486 (6)	C13—C14	1.401 (7)
C6—C7	1.390 (6)	C14—N1	1.155 (6)
C6—H5	1.0007

C2—C1—Br	113.3 (4)	C2—C7—H6	122.6
C2—C1—H1A	109.8	C6—C7—H6	115.5
Br—C1—H1A	106.2	C9—C8—C13	117.7 (4)
C2—C1—H1B	113.8	C9—C8—C5	119.8 (4)
Br—C1—H1B	99.5	C13—C8—C5	122.5 (4)
H1A—C1—H1B	113.7	C10—C9—C8	121.0 (5)
C7—C2—C3	119.1 (4)	C10—C9—H9	116.5
C7—C2—C1	120.3 (4)	C8—C9—H9	121.5
C3—C2—C1	120.6 (5)	C11—C10—C9	120.7 (5)
C2—C3—C4	120.2 (5)	C11—C10—H10	122.3
C2—C3—H3	116.1	C9—C10—H10	117.0
C4—C3—H3	123.7	C10—C11—C12	120.3 (5)
C3—C4—C5	120.3 (4)	C10—C11—H11	116.0
C3—C4—H4	116.5	C12—C11—H11	123.5
C5—C4—H4	123.1	C11—C12—C13	120.2 (5)
C6—C5—C4	118.9 (4)	C11—C12—H12	121.2
C6—C5—C8	121.1 (4)	C13—C12—H12	118.3
C4—C5—C8	120.1 (4)	C14—C13—C12	118.3 (5)
C5—C6—C7	119.7 (5)	C14—C13—C8	121.4 (4)
C5—C6—H5	123.8	C12—C13—C8	120.2 (4)
C7—C6—H5	116.3	N1—C14—C13	177.7 (6)
C2—C7—C6	121.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Brⁱ	0.93	2.82	3.699 (6)	158
C1—H1A···N1ⁱⁱ	1.08	2.61	3.634 (8)	159
C9—H9···Brⁱⁱⁱ	0.96	3.05	3.750 (6)	131

Symmetry codes: (i) x, y, z−1; (ii) −x+3/4, y+1/4, z+3/4; (iii) −x+1/2, −y+1, z+1/2.

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4′-Bromo­methyl­bi­phenyl-2-carbo­nitrile

Supporting information

Key indicators

checkCIF/PLATON results

4′-Bromomethylbiphenyl-2-carbonitrile